Aluminium lithium hydride → [6-(3-Methoxyphenyl)-2-(morpholin-4-ylethyl)pyrimidin-4-yl]-3-pyridylamine

HRID 499039Notes

Reaction equation

HRID 499039 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([C:15]2[N:20]=[C:19]([CH2:21][C:22]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=O)[N:18]=[C:17]([NH:30][C:31]3[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=3)[CH:16]=2)[CH:12]=[CH:13][CH:14]=1>C1COCC1>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([C:15]2[N:20]=[C:19]([CH2:21][CH2:22][N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[N:18]=[C:17]([NH:30][C:31]3[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=3)[CH:16]=2)[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 597896702-[6-(3-Methoxyphenyl)-4-(3-pyridylamino)pyrimidin-2-yl]-1-morpholin-4-ylethan-1-one

Product 1

HCID 59789786[6-(3-Methoxyphenyl)-2-(morpholin-4-ylethyl)pyrimidin-4-yl]-3-pyridylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A dry round bottom flask is charged with LiAlH4 (4 eq), and dry THF is added. The suspension is cooled down to 0° C. and a solution of compound 10 in THF is added dropwise. The reaction mixture is stirred 4 h at room temperature then cooled down to 0° C. and quenched with water, followed by 10% NaOH and then water again. The mixture is stirred overnight and the solid is filtered off. The aqueous phase is extracted with CH2Cl2, the organic extracts are collected and dried (Na2SO4). After evaporation of the solvent under reduced pressure and purification by reverse phase preparatory HPLC [6-(3-methoxyphenyl)-2-(2-morpholin-4-ylethyl)pyrimidin-4-yl]-3-pyridylamine 11 is obtained.

Workup

  1. additionis added
  2. temperaturethen cooled down to 0° C.
  3. customquenched with water
  4. stirringThe mixture is stirred overnight
  5. filtrationthe solid is filtered off
  6. extractionThe aqueous phase is extracted with CH2Cl2
  7. customthe organic extracts are collected
  8. dry with materialdried (Na2SO4)
  9. customAfter evaporation of the solvent
  10. customunder reduced pressure and purification by reverse phase preparatory HPLC [6-(3-methoxyphenyl)-2-(2-morpholin-4-ylethyl)pyrimidin-4-yl]-3-pyridylamine 11
  11. customis obtained

Sources & evidence

ORD record
ord-5142788ad8b549f5bee6ddf729788f5a
Source dataset
uspto-grants-2010_08
Patent number
US07767669B2

Reaction notes

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